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Unexpected Z-stereoselectivity in the Ramberg-Bäcklund reaction of diarylsulfones leading to cis-stilbenes: the effect of aryl substituents and application in the synthesis of the integrastatin nucleus

Jonathan S. Foot, Gerard M. P. Giblin, A. C. Whitwood and R. J. K. Taylor*

*Department of Chemistry, University of York, Heslington, York YO10 5DD, UK, Email: rjkt1york.ac.uk

J. S. Foot, G. M. P. Giblin, A. C. Whitwood, R. J. K. Taylor, Org. Biomol. Chem., 2005, 3, 756-763.

DOI: 10.1039/b418426b (free Supporting Information)


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Abstract

With certain substituent patterns, benzyl benzyl sulfone systems give unexpectedly high Z-stereoselectivity in the Meyers variant of the Ramberg-Bäcklund reaction. A range of sulfones were explored to rationalize this unprecedented selectivity for Z-stilbene systems.

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proposed π-stacking - Reproduced by permission of The Royal Society of Chemistry



Key Words

Ramberg-Bäcklund Reaction, Stilbenes


ID: J52-Y2005-3240